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WO2015136551A2 - Complexe moléculaire d'épigallocatéchine-3-gallate et son procédé de production - Google Patents

Complexe moléculaire d'épigallocatéchine-3-gallate et son procédé de production Download PDF

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Publication number
WO2015136551A2
WO2015136551A2 PCT/IN2015/000122 IN2015000122W WO2015136551A2 WO 2015136551 A2 WO2015136551 A2 WO 2015136551A2 IN 2015000122 W IN2015000122 W IN 2015000122W WO 2015136551 A2 WO2015136551 A2 WO 2015136551A2
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WO
WIPO (PCT)
Prior art keywords
gallate
epigallocatechin
molecular complex
mixture
sucralose
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PCT/IN2015/000122
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English (en)
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WO2015136551A3 (fr
Inventor
Saikat Roy
Anil Kumar
Jose DAVID
Bhargav MESHIYA
Ravindra BARHALIKAR
Silpi DATTA
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Tata Chemicals Limited
Tata Global Beverages Limited
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Publication of WO2015136551A2 publication Critical patent/WO2015136551A2/fr
Publication of WO2015136551A3 publication Critical patent/WO2015136551A3/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/549—Sugars, nucleosides, nucleotides or nucleic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system

Definitions

  • the present disclosure relates to molecular complex of Epigallocatechin-3- gallate and process for production thereof.
  • Epigallocatechin-3 -gallate (EGCG), the main and most important polyphenol in green tea ⁇ Camellia sinensis), has shown numerous health promoting effects.
  • Epigallocatechin gallate belongs to the family of catechins. It contains 3 phenol rings and has very strong antixoidant properties.
  • EGCG lacks long-term stability and is very sensitive to light and heat and also possess a very astringent and bitter taste, which limits its use in food or in oral medications.
  • EGCG gallocatechin gallate
  • ECG Epicatechin gallate
  • ECG Epigallocatechin
  • GC Gallocatechin
  • EGCG For food, beverages and other oral applications we need stable and tastier EGCG.
  • a stable and tasty variant of EGCG would allow higher incorporation in enhancing the polyphenolic or antioxidant content without affecting the organoleptic properties.
  • a molecular complex of Epigallocatechin-3-gallate comprises Epigallocatechin-3-gallate and a molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic Acid, Carnosine, Maltose, Maltitol, Fructo-oligosaccharides and mixture thereof.
  • the molecular complex further comprises the improved stability in hot water.
  • a process for preparing a molecular complex of Epigallocatechin-3-gallate and a molecular complex comprises Epigallocatechin-3-gallate and a molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic Acid, Carnosine, Maltose, Maltitol, Fructo-oligosaccharides and mixture thereof is disclosed.
  • the process comprises mixing Epigallocatechin-3- gallate and the molecular complex former in any molar ratios between 1 :48 to 4: 1 , followed by grinding to form a dry mixture; adding a solvent to the dry mixture followed by grinding to obtain a wet mixture; and air drying the wet mixture to obtain the molecular complex.
  • Figure 1 illustrates the PXRD pattern of Epigallocatechin-3-gallate, Trehalose and Epigallocatechin-3-gallate : Trehalose molecular complex.
  • Figure 2 illustrates the PXRD pattern of Epigallocatechin-3-gallate, Sucralose and Epigallocatechin-3-gallate : Sucralose molecular complex.
  • Figure 3 illustrates the PXRD pattern of Epigallocatechin-3-gallate, Glutamic acid and Epigallocatechin-3-gallate : Glutamic acid molecular complex.
  • FIG. 4 illustrates the PXRD pattern of Epigallocatechin-3-gallate
  • Glutamine and Epigallocatechin-3-gallate Glutamine molecular complex.
  • Figure 5 illustrates the PXRD pattern of Epigallocatechin-3-gallate, Glycine and Epigallocatechin-3-gallate : Glycine Molecualr Complex.
  • Figure 6 illustrates the PXRD pattern of Epigallocatechin-3-gallate, Lipoic Acid and Epigallocatechin-3-gallate-Lipoic acid molecular complex.
  • Figure 7 illustrates the PXRD Pattern of Epigallocatechin-3-gallate, Carnosine and Epigallocatechin-3-gallate-Carnosine molecular complex.
  • Figure 8 illustrates the PXRD Pattern of Epigallocatechin-3-gallate, Maltose and Epigallocatechin-3-gallate : Maltose molecular complex.
  • FIG. 9 illustrates the PXRD pattern of Epigallocatechin-3-gallate
  • Maltitol and Epigallocatechin-3-gallate Maltitol molecular complex.
  • Figure 10 illustrates the PXRD pattern of Epigallocatechin-3-gallate, Nystose and Epigallocatechin-3-gallate : Nystose molecular complex.
  • Figure 11 illustrates the IR spectra of Epigallocatechin-3-gallate, Trehalose and Epigallocatechin-3-gallate : Trehalose molecular complex.
  • Figure 12 illustrates the IR Spectra of Epigallocatechin-3-gallate, Sucralose and Epigallocatechin-3-gallate : Sucralose molecular complex.
  • Figure 13 illustrates the IR Spectra of Epigallocatechin-3-gallate, Glutamic acid and Epigallocatechin-3-gallate : Glutamic acid molecular complex.
  • Figure 14 illustrates the IR Spectra of Epigallocatechin-3-gallate
  • Glutamine and Epigallocatechin-3-gallate Glutamine molecular complex.
  • Figure 15 illustrates the IR Spectra of Epigallocatechin-3-gallate, Glycine and Epigallocatechin-3-gallate : Glycine molecular complex.
  • Figure 16 illustrates the IR Specra of Epigallocatechin-3-gallate, Lipoic Acid and Epigallocatechin-3-gallate : Lipoic acid molecular complex.
  • Figure 17 illustrates the IR Spectra of Epigallocatechin-3-gallate, Carnosine and Epigallocatechin-3-gallate : Carnosine molecular complex.
  • Figure 18 illustrates the IR Spectra of Epigallocatechin-3-gallate, Maltose and Epigallocatechin-3-gallate : Maltose molecular complex.
  • Figure 19 illustrates the IR Spectra of Epigallocatechin-3-gallate, Maltitol and Epigallocatechin-3-gallate : Maltitol molecular complex.
  • Figure 20 illustrates the IR Spectra of Epigallocatechin-3-gallate, Nystose and Epigallocatechin-3-gallate : Nystose molecular complex.
  • Figure 21 illustrates the DSC profile of. Epigallocatechin-3-gallate, Trehalose and Epigallocatechin-3-gallate : Trehalose molecular complex.
  • Figure 22 illustrates the DSC profile of Epigallocatechin-3-gallate, Sucralose and Epigallocatechin-3-gallate : Sucralose molecular complex.
  • Figure 23 illustrates the DSC profile of Epigallocatechin-3-gallate, Glutamic acid and Epigallocatechin-3-gallate : Glutamic acid molecular complex.
  • Figure 24 illustrates the DSC profile of Epigallocatechin-3-gallate, Glutamine and Epigallocatechin-3-gallate : Glutamine molecular complex.
  • Figure 25 illustrates the DSC profile of Epigallocatechin-3-gallate, Glycine and Epigallocatechin-3-gallate : Glycine molecualr Complex.
  • Figure 26 illustrates the DSC profile of Epigallocatechin-3-gallate, Lipoic Acid and Epigallocatechin-3-gallate : Lipoic acid molecular complex.
  • Figure 27 illustrates the DSC profile of Epigallocatechin-3-gallate, Carnosine and Epigallocatechin-3-gallate : Carnosine molecular complex.
  • Figure 28 illustrates the DSC profile of Epigallocatechin-3-gallate, Maltose and Epigallocatechin-3-gallate : Maltose molecular complex.
  • Figure 29 illustrates the DSC profile of Epigallocatechin-3-gallate, Maltitol and Epigallocatechin-3-gallate : Maltitol molecular complex.
  • Figure 30 illustrates the DSC profile of Epigallocatechin-3-gallate, Nystose and Epigallocatechin-3-gallate : Nystose molecular complex.
  • Table 1 exhibits the IR stretching frequency of Epigallocatechin-3-gallate, Trehalose and Epigallocatechin-3-gallate: Trehalose molecular complex
  • Table 2 exhibits the IR stretching frequency of Epigallocatechin-3-gallate, Sucralose and Epigallocatechin-3-gallate: Sucralose molecular complex.
  • Table 3 exhibits the IR stretching frequency of Epigallocatechin-3-gallate, Glutamic acid and Epigallocatechin-3-gallate: Glutamic acid molecular complex.
  • Table 4 exhibits the IR stretching frequency of Epigallocatechin-3-gallate, Glutamine and Epigallocatechin-3-gallate: Glutamine molecular complex.
  • Table 5 exhibits the IR stretching frequency of Epigallocatechin-3 -gallate, Glycine and Epigallocatechin-3-gallate: Glycine.
  • Table 6 exhibits the IR stretching frequency of Epigallocatechin-3 -gallate, 115 Lipoic acid and Epigallocatechin-3 -gallate: Lipoic acid molecular complex.
  • Table 7 exhibits the IR stretching frequency of Epigallocatechin-3 -gallate, Carnosine and Epigallocatechin-3 -gallate: Carnosine molecular complex.
  • Table 8 exhibits the IR stretching frequency of Epigallocatechin-3 -gallate, Maltose and Epigallocatechin-3 -gallate: Maltose molecular complex.
  • Maltitol and Epigallocatechin-3-gallate Maltitol molecular complex.
  • Table 10 exhibits the IR stretching frequency of Epigallocatechin-3 - gallate, FOS (Nystose) and Epigallocatechin-3-gallate: FOS (Nystose) molecular complex.
  • Table 11 illustrates the HPLC profile of hot water stability of standard
  • Table 12 illustrates the HPLC profile oof standard Epigallocatechin-3 - gallate and Epigallocatechin-3-gallate in molecular complexes in beverages after storage condition.
  • the disclosure relates to molecular complexes of Epigallocatechin-3- gallate and a molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic Acid, Carnosine, Maltose, Maltitol, Fructo-oligosaccharides (FOS) and mixture thereof.
  • a molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic Acid, Carnosine, Maltose, Maltitol, Fructo-oligosaccharides (FOS) and mixture thereof.
  • Molecular complex herein refers to a substance which is solid form or solid formulations, which comprises in its with at least two substances which interact with each other through hydrogen bonding or any other non- covalent interactions to form molecular complex including co-crystals, solvates, hydrates, eutectic combinations or solid solutions, in which at least one of the substance is present in the solid form.
  • Epigallocatechin-3-gallate refers to all polymorphs, solvates, and hydrates of the substance having the formula (I):
  • the molecular complex former compound selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic Acid, Carnosine, Maltose, Maltitol and FOS refers to all polymorphs, solvates, and hydrates of the substance having the formula (II):
  • n 3:
  • Fructo-oligosaccharides are oligomers of fructose having degree of
  • GF2 kestose
  • GF3 nystose
  • GF4 fructofuranosylnystose
  • 190 complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) is illustrated in figures 1 to 10.
  • the infrared absorption profile of molecular complex of Epigallocatechin-3-gallate with molecular 195 complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine,
  • Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) is illustrated in figures 1 1 to 20.
  • Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) was measured through endothermic/exothermic transition by differential scanning calorimetry is given in figures 21 to 30.
  • the stoichiometric ratio of Epigallocatechin- 205 3-gallate molecular complex former selected from Trehalose, Sucralose,
  • Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) in the molecular complex of Epigallocatechin-3-gallate and molecular complex former is any molar ratios between 1 :48 to 4: 1, preferably 1 :4 to 4: l .
  • Epigallocatechin-3-gallate with molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) has improved hot water stability.
  • molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) has improved hot water stability.
  • the molecular complex is at least 15% more stable than the
  • the molecular complex of Epigallocatechin-3-gallate with molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) has improved taste.
  • molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) has improved taste.
  • the molecular complex has the masking effect on the bitterness of the standard Epigallocatechin-3-gallate.
  • the molecular complex of Epigallocatechin-3-gallate with molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine,
  • the invention provides a pharmaceutical, foodstuff, nutritional supplement, and nutritional composition comprising molecular complex of Epigallocatechin-3-gallate and molecular complex former
  • 230 selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) as described herewith.
  • the process comprises of preparing a mixture of Epigallocatechin-3- gallate and molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol
  • the grinding may be carried out in any suitable apparatus for grinding 240 solids.
  • Such apparatus includes but is not limited to mortar mills, vibrator mills or ball mills.
  • the ground mixture is heated at 60 to 80°C using but not limited to temperature control water bath with or without vacuum.
  • the heating may be carried out under an inert atmosphere.
  • Epigallocatechin-3-gallate and molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose).
  • the process comprises of admixing Epigallocatechin-3-gallate and molecular complex
  • 250 former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) in a 1 : 1 stoichiometric ratio to form a dry mixture, grinding said dry mixture for a predetermined period of time, adding few drops of solvent to make it wet and grinding the wet mixture for a predetermined period of time under inert condition,
  • the wet grinding and heating is carried out under nitrogen atmosphere.
  • the grinding of the dry mixture is carried out for 1 to 20 minutes.
  • the grinding of the wet mixture may be 265 carried out for 1-20 minutes.
  • the grinding is carried out in any suitable apparatus for grinding solids.
  • apparatus includes but is not limited to mortar mills, vibrator mills or ball mills.
  • the solvent is any suitable solvent 270 including but not limited to water, acetonitrile, ethanol, methanol, ethyl acetate, acetone or their mixture.
  • the amount of solvent added is in a range of 0.1 ml to 10 ml per 1 to 10 gram of combined weight of Epigallocatechin-3-gallate and molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS 275 (Nystose).
  • Epigallocatechin-3-gallate and molecular complex former selected from 280 Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) were weighed in a 1 : 1 molar ratio for different experiments and ground using mortar and pestle for 5 minutes to make a homogenous mixture followed making paste under inert condition (Nitrogen atmosphere) with few drops of water added to it. Heating the mixture around 70- 285 75 °C temperature control water bath for 15-20 min under vacuum in a rotary evaporator. The resulted material was cooled to room temperature to obtain the molecular complex.
  • Powder X-ray Diffraction (PXRD) profiles were obtained using
  • Molecular complexes of Epigallocatechin-3-gallate and molecular 295 complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) gave different PXRD profile than pure Epigallocatechin-3-gallate and molecular complex former.
  • Figures 1 to 10 illustrate a comparative PXRD profile of samples of molecular complexes of Epigallocatechin-3-gallate with molecular complex 300 former along with pure Epigallocatechin-3-gallate and pure molecular complex former.
  • Table 1 to 10 exhibit the major IR peaks of the samples of molecular complexes of Epigallocatechin-3-gallate and molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose).
  • DSC Differential Scanning Calorimetric
  • Figures 21 to 30 illustrate the comparative DSC profile of samples of molecular complexes of Epigallocatechin-3-gallate with molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, 325 Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) along with pure Epigallocatechin-3-gallate and molecular complex former.
  • molecular complex former selected from Trehalose, Sucralose, Glutamic Acid, Glutamine, 325 Glycine, Lipoic acid, Carnosine, Maltose, Maltitol and/or FOS (Nystose) along with pure Epigallocatechin-3-gallate and molecular complex former.
  • Example 5 Stability of Epigallocatechin-3-galIate in hot water:
  • Epigallocatechin-3-gallate standard and molecular complex of Epigallocatechin-3 - gallate and Trehalose (1 : 1) and molecular complex of Epigallocatechin-3-gallate
  • HPLC 340 chromatography
  • Epigallocatechin-3 -gallate was prepared using 1 gram equivalent of 345 Epigallocatechin-3-gallate.
  • Epigallocatechin-3-gallate standard and molecular complex of Epigallocatechin-3 -gallate and Trehalose (1 : 1), molecular complex of Epigallocatechin-3-gallate and Sucralose (1 : 1) and molecular complex of Epigallocatechin-3 -gallate and Carnosine (1 : 1) were weighed as 1 gm equivalent of Epigallocatechin-3 -gallate separately and taken in in separate flask as a 350 separate experiment sample.
  • the molecular complex of Epigallocatechin-3-gallate has better stability, lesser bitterness and is tastier.
  • a stable and tasty variant of EGCG would allow higher 365 incorporation in enhancing the polyphenolic or antioxidant content without affecting the organoleptic properties in food, beverages and other oral applications.

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Abstract

La présente invention concerne un complexe moléculaire d'Épigallocatéchine-3-gallate. Le complexe moléculaire comprend de l'Épigallocatéchine-3-gallate et un agent complexant moléculaire choisi parmi le Tréhalose, le Sucralose, l'Acide Glutamique, la Glutamine, la Glycine, l'Acide Lipoïque, la Carnosine, le Maltose, le Maltitol, les Fructo-oligosaccharides et un mélange de ceux-ci.
PCT/IN2015/000122 2014-03-12 2015-03-11 Complexe moléculaire d'épigallocatéchine-3-gallate et son procédé de production WO2015136551A2 (fr)

Applications Claiming Priority (2)

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IN825/MUM/2014 2014-03-12
IN825MU2014 2014-03-12

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WO2015136551A2 true WO2015136551A2 (fr) 2015-09-17
WO2015136551A3 WO2015136551A3 (fr) 2016-01-14

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3488849A1 (fr) * 2017-11-23 2019-05-29 Assistance Publique, Hopitaux De Paris Solution d'épigallocathechin gallate
CN110049688A (zh) * 2016-12-15 2019-07-23 国际香料和香精公司 用于掩味的新型组合物
JP2022534293A (ja) * 2019-05-29 2022-07-28 アシスタンス ピュブリク－オピトー ドゥ パリ 緑茶カテキン共融系

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WO2008153938A2 (fr) * 2007-06-06 2008-12-18 University Of South Florida Compositions de cristal d'épigallocatéchine-3-gallate
US20100055205A1 (en) * 2008-08-29 2010-03-04 Kristina Mains Functional consumable compositions for promoting skin health and methods for using the same

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110049688A (zh) * 2016-12-15 2019-07-23 国际香料和香精公司 用于掩味的新型组合物
CN110049688B (zh) * 2016-12-15 2023-01-03 国际香料和香精公司 用于掩味的新型组合物
EP3488849A1 (fr) * 2017-11-23 2019-05-29 Assistance Publique, Hopitaux De Paris Solution d'épigallocathechin gallate
WO2019101777A1 (fr) * 2017-11-23 2019-05-31 Assistance Publique - Hopitaux De Paris Solution de gallate d'épigallocatéchine
JP2021504460A (ja) * 2017-11-23 2021-02-15 アシスタンス ピュブリク−オピトー ドゥ パリＡｓｓｉｓｔａｎｃｅ Ｐｕｂｌｉｑｕｅ − Ｈｏｐｉｔａｕｘ Ｄｅ Ｐａｒｉｓ 没食子酸エピガロカテキン溶液
US11938113B2 (en) 2017-11-23 2024-03-26 Assistance Publique—Hopitaux de Paris Epigallocathechin gallate solution
JP2022534293A (ja) * 2019-05-29 2022-07-28 アシスタンス ピュブリク－オピトー ドゥ パリ 緑茶カテキン共融系

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